Work on the stereospecific, total synthesis of the macrolide antibiotic methymycin will be continued. Construction of the methynolide spine in two segments is envisaged, and immediate attention will be given to synthesis of the segment corresponding to carbons 1-7 of the macrolide. The approach will follow a plan developed in a model system, involving construction of an 8-oxabicyclo(3.2.1)octane system, the bicyclic framework providing the rigid platform upon which to erect the appropriate functionality in the proper stereochemical sense. Subsequently, the second segment corresponding to carbons 8-11 of methynolide will be made and joined to the larger segment by means of a Wittig reaction. Completion of the synthesis involves lactonization of the alpha, w-hydroxyacid produced by this scheme along lines already developed for a model system.